CN1613921A - Ultraviolet light curing cathodic electrophoretic coating and preparation thereof - Google Patents
Ultraviolet light curing cathodic electrophoretic coating and preparation thereof Download PDFInfo
- Publication number
- CN1613921A CN1613921A CN 200410054389 CN200410054389A CN1613921A CN 1613921 A CN1613921 A CN 1613921A CN 200410054389 CN200410054389 CN 200410054389 CN 200410054389 A CN200410054389 A CN 200410054389A CN 1613921 A CN1613921 A CN 1613921A
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- CN
- China
- Prior art keywords
- ultraviolet light
- acrylic resin
- light polymerization
- cathode electrophoresis
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims description 19
- 239000011248 coating agent Substances 0.000 title description 8
- 238000000576 coating method Methods 0.000 title description 8
- 238000001962 electrophoresis Methods 0.000 claims abstract description 33
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 30
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 30
- 239000003999 initiator Substances 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000178 monomer Substances 0.000 claims description 35
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- -1 acrylic ester Chemical class 0.000 claims description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 17
- 229920002554 vinyl polymer Polymers 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 4
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 239000005056 polyisocyanate Substances 0.000 claims description 3
- 229920001228 polyisocyanate Polymers 0.000 claims description 3
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical group [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 238000009775 high-speed stirring Methods 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 2
- 125000001302 tertiary amino group Chemical group 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000003504 photosensitizing agent Substances 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 6
- 238000004070 electrodeposition Methods 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000007888 film coating Substances 0.000 abstract 1
- 238000009501 film coating Methods 0.000 abstract 1
- 230000035807 sensation Effects 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000000975 dye Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 150000003512 tertiary amines Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000007701 flash-distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- GABHINZQJRXISH-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.CC1CCCCC1 Chemical compound C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.CC1CCCCC1 GABHINZQJRXISH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UFQOAIGWDYZJJO-UHFFFAOYSA-N n-methylmethanamine;n-propylprop-2-enamide Chemical compound CNC.CCCNC(=O)C=C UFQOAIGWDYZJJO-UHFFFAOYSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
- CLHYKAZPWIRRRD-UHFFFAOYSA-N 1-hydroxypropane-1-sulfonic acid Chemical compound CCC(O)S(O)(=O)=O CLHYKAZPWIRRRD-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- LPNSCOVIJFIXTJ-UHFFFAOYSA-N 2-methylidenebutanamide Chemical compound CCC(=C)C(N)=O LPNSCOVIJFIXTJ-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- VUZHZDBMVSHDRE-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OCCCOC(=O)C=C VUZHZDBMVSHDRE-UHFFFAOYSA-N 0.000 description 1
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- WQUYGVLLSSYSRD-UHFFFAOYSA-N C(C=C)(=O)OCC(C)O.CC=CC(=O)O Chemical compound C(C=C)(=O)OCC(C)O.CC=CC(=O)O WQUYGVLLSSYSRD-UHFFFAOYSA-N 0.000 description 1
- IPCWTALQCRIHLP-UHFFFAOYSA-N C(C=C)(=O)OCCCO.CC=CC(=O)O Chemical compound C(C=C)(=O)OCCCO.CC=CC(=O)O IPCWTALQCRIHLP-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N beta-hydroxyethanesulfonic acid Natural products OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001652 electrophoretic deposition Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical group CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JOLNFGHBHWJGBH-UHFFFAOYSA-N n-ethylprop-2-enamide;n-methylmethanamine Chemical compound CNC.CCNC(=O)C=C JOLNFGHBHWJGBH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- PWYYERNADDIMJR-UHFFFAOYSA-N pentyl but-2-enoate Chemical compound CCCCCOC(=O)C=CC PWYYERNADDIMJR-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
Abstract
A UV solidified cathode electrophoresis covering material includes: 100 portion of etheny which can solidify the UV, the modified acrylic resin which has the amide of electrodeposition cathodic, and 0.1-10 portion of one or many light sensation initiator which can absorb 200-400nm UV. The surface of film coating is smooth and has good attachment to the backing. Especially it can solidify the UV in the normal temperature. So it can be used to the thermo-sensitive material.
Description
Technical field
The present invention relates to a kind of coating, especially, relate to a kind of ultraviolet light polymerization cathode electrophoresis dope and preparation method thereof.
Background technology
Cathode electrophoresis dope is since the development seventies in 20th century and obtaining industrial applications, with its superior corrosion resistance, high throwing power, high coulomb efficiency, do not dissolve advantages such as coated article, tank liquor are stable, level of automation height, obtain widespread use in industries such as automotive industry, household electrical appliance, instrument, military project, building materials, progressively replace anode electrophoresis dope, and become one of most important application mode in the world today.
Present cathode electrophoresis dope adopts the thermofixation mode crosslinked, and not only the storing temperature height is generally 170~180 ℃, and storing time is long, generally greater than 20 minutes.Even the low temperature thermofixation cathode electrophoresis dope that latest developments are got up, its solidification value also is higher than 120 ℃, this has just limited its application in the thermo-sensitivity plastic basis material greatly, and most electrophoretic paint is in curing process, can discharge small organic molecule, contaminate environment can discharge small molecules as present widely used blocked isocyanate curing agent in solidification process.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, provide a kind of by the acrylic resin modified ultraviolet light polymerization cathode electrophoresis dope of making.
This goal of the invention is achieved through the following technical solutions:.
The present invention also aims to provide a kind of preparation method of above-mentioned ultraviolet light polymerization cathode electrophoresis dope.
This goal of the invention is achieved through the following technical solutions:
The present invention has following technique effect: room temperature fast-curing, energy-conservation, environmental friendliness both can be used for the conventional metals base material, can be used for the plastic basis material of thermo-sensitivity again.
Embodiment
The acrylic resin molecular weight is 2000~30000, has tertiary amine groups and hydroxyl on the side chain.It is formed by the copolymerization under the initiator effect of following several monomers, described monomer comprises that (a) contains (methyl) acrylic ester monomer of tertiary amine groups, its content is 5~26wt%, (b) (methyl) acrylic ester monomer of hydroxyl, its content is 15~30wt%, and (c) other acrylic ester monomer, its content are 45~70wt%, (d) vinyl monomer, its content are 0~30wt%.
The described unsaturated monomer (a) that contains tertiary amine groups, comprise (methyl) vinylformic acid dimethylamine ethyl ester, (methyl) vinylformic acid diethylamine ethyl ester, (methyl) vinylformic acid dimethylamine n-propyl, (methyl) vinylformic acid diethylamine n-propyl, (methyl) vinylformic acid diethylamine methyl esters, N dimethylamine ethyl acrylamide, N dimethylamine ethyl-methyl acrylamide, N dimethylamine base ethyl acrylamide, N dimethylamine ethyl-methyl acrylamide etc., and other contains the vinyl substituted heterocycle of tertiary amine groups, as vinyl pyridine, N-vinyl imidazole, N-vinyl pyrrolidone etc.
The unsaturated comonomer of above-mentioned hydroxyl (b) comprises (methyl) vinylformic acid-2-hydroxyl ethyl ester, (methyl) vinylformic acid-3-hydroxypropyl acrylate, (methyl) vinylformic acid-4-hydroxy butyl ester, (methyl) vinylformic acid-2-hydroxypropyl acrylate.
Above-mentioned other acrylic ester monomer (c) comprises (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) vinylformic acid n-pentyl ester, the just own ester of (methyl) vinylformic acid, (methyl) ethyl acrylate etc.
Above-mentioned vinyl monomer (d) comprises vinyl cyanide, vinylbenzene, vinyl acetate etc.
Monomer (a) contains tertiary amine groups, and it gives resin cationic electrodeposition characteristic, and the content in comonomer is 5~26wt%.When content is too low, acrylic resin modified can not in water, the dispersion well, can not form uniform electrodeposition coating; When content is too much, can produce undesired deposition.
(methyl) acrylic ester monomer (b) of hydroxyl and other monomer copolymerizable, can improve the dispersiveness of resin in water on the one hand, improve the sticking power of itself and substrate, on the other hand can with the isocyanate reaction that contains vinyl, make the vinyl of introducing uV curable in the resin.Its content is 15~30wt%, but content is when too much, easily make electrophoresis film in water-content increase.
Monomer (c) give film snappiness and smoothness, and its consumption can be adjusted in very wide scope as required.
Monomer (d) can improve water tolerance, the chemical proofing of filming, reduce cost.Its consumption is too much, and the fragility of filming is increased.
Can select suitable solvent, adopt solution polymerization process to prepare acrylic resin.Solvent can adopt aromatic hydrocarbon solvents such as toluene, dimethylbenzene, ketones solvents such as methyl ethyl ketone.Initiator amount is 0.5~5wt% of comonomer, can adopt azo or peroxide initiator, perhaps mixed initiator.The number-average molecular weight of the acrylic resin of copolymerization gained is between 2000~30000.
The acrylic resin that makes is under catalyst actions such as zinc octoate, ferric acetyl acetonade, dibutyl tin laurate, organo-bismuth, hydroxyl in the acrylic resin obtains acrylic resin modified with the isocyanato reaction that contains in the isocyanic ester of vinyl, make in the resin vinyl of introducing uV curable, wherein in the acrylic resin in hydroxyl and the isocyanic ester mol ratio of isocyanato be 1: 0.3~1.0.Consumption as if the isocyanic ester that contains vinyl is very few, then is unfavorable for the ultraviolet light polymerization that electrophoresis is filmed; Consumption is too much, then influences the sticking power of coating to base material.
Above-mentioned isocyanic ester can be the monoisocyanates that contains vinyl, as a pseudoallyl-α, α-Er Jiajibianji isocyanic ester (TMI), methacrylic acid-2-isocyanato ethyl ester (MOI), it also can be the polyisocyanates that contains the different isocyanato of active degree, as tolylene diisocyanate (TDI), isophorone diisocyanate (IPDI), 2,6-two isocyanato methyl caproates (LDI), 2,2,4-trimethylammonium hexamethylene diisocyanate (TMDI), Methylcyclohexyl diisocyanate (HTDI), the unsaturated monomer such as the 2-hydroxyethyl methacrylate of dimer acid diisocyanate (DDI) etc. and hydroxyl, the product of reaction such as methacrylic acid-3-hydroxypropyl acrylate.
The ultraviolet light polymerization cathode electrophoresis dope also contains photoinitiator.The photoinitiator that is fit to comprises benzophenone and derivative, phenylbenzyl ketone and derivative thereof, methyl phenyl ketone and derivative thereof, st-yrax ethers and derivative thereof etc.They both can use separately, also can mix use, and its consumption is 0.5~10% of a resin quality.
Acrylic resin modified with acid neutralization preparation.The used acid that neutralizes comprises organic acid and mineral acid, organic acid such as formic acid, acetate, lactic acid, propionic acid, butyric acid, methanesulfonic, ethane sulfonic acid, propane sulfonic acid, hydroxyethanesulfonic acid, hydroxypropanesulfonic acid etc., mineral acid example hydrochloric acid, sulfuric acid, phosphoric acid etc.The consumption of acid changes with the content of tertiary amine groups in the resin, but resin is evenly dispersed in the water, and the degree of neutralization of tertiary amine groups is generally between 0.5~1.0.
As required, in the ultraviolet light polymerization cathode electrophoresis dope, add dyestuff or pigment and other additive such as tensio-active agent, antioxidant etc.Preferred dyestuff such as mordanting dye.Pigment comprises pigment dyestuff and mineral dye, pigment dyestuff such as azo-type, phthalein cyanogen type, metal complex salt etc.; Metallic compounds such as mineral dye such as titanium oxide, ferric oxide, barium sulfate.Carbon black also can be used as pigment, and its consumption should be less than the 20wt% of resin.
The acid neutral is acrylic resin modified, and to be diluted to solids constituent content with deionized water be 5~30wt%, and regulating the pH value is 5~7, and high-speed stirring forms stable water dispersion.In the electrophoresis groove liquid temperature is that 18~30 ℃, voltage are to carry out electrophoretic deposition under the condition of 10~250V, obtains filming of even compact.After the small amount of moisture during flash distillation is removed and filmed, the crosslinked ultraviolet light polymerization ability cathode electrophoresis that obtains of ultraviolet light polymerization is filmed at normal temperatures.
The invention will be further described below in conjunction with embodiment, but the present invention is not limited thereto.
Embodiment 1
One, the preparation of acrylic resin
The Diisopropyl azodicarboxylate that accounts for monomer mass 3% is dissolved in the monomer, wherein methyl methacrylate, vinylbenzene, butyl methacrylate and 2-hydroxyethyl methacrylate consumption are respectively 79,21,22 and 44.4g, and the consumption of methacrylic diethylammonium salt ethyl ester is 16.8g.Slowly splash in the four-hole boiling flask that agitator, reflux condensing tube, thermometer are housed at 75 ℃ of following monomers, solvent is a butanone, and its consumption is 1.5 times of monomer mass, reacts 4 hours, and monomer conversion is reached more than 98%.
Two, acrylic resin modified preparation
In the synthetic acrylic resin, add catalyzer 0.5wt% dibutyl tin laurate, slowly drip pseudoallyl-α between 42.4g, α-Er Jiajibianji isocyanic ester down at 60 ℃, reacted 3 hours, add an amount of dehydrated alcohol, remove unreacted isocyanic ester, vacuum extracts solvent.
Three, the preparation of ultraviolet light polymerization cathod coating
The adding mass ratio is 1: 1 2-hydroxy-2-methyl Propiophenone and a 1-methylcyclohexane benzophenone photoinitiator in acrylic resin modified, its consumption is the 1.5wt% of resin, is 6.0 with lactic acid neutralization to the pH value, and to be diluted to solid content with deionized water be 15%, is mixed with the ultraviolet light polymerization cathode electrophoresis dope through high speed dispersion.
Four, ultraviolet light polymerization cathode electrophoresis dope Performance Detection
With the preparation the ultraviolet light polymerization cathode electrophoresis dope as electrophoresis groove liquid, under 25 ℃ of temperature, voltage 20V, electrophoretic painting is carried out on the stainless steel plate surface.Stainless steel plate after the application was 60 ℃ of following flash distillations 10 minutes, and curing cross-linked is 55 seconds under room temperature, 1kW high pressure Hg lamp irradiation.Recording coating thickness is 25 μ m, appearance of film light, fine and smooth smooth, and pencil hardness>6H, the two-way wiping examination of acetone is filmed and is not seen the loss of gloss phenomenon 150 times, shows that curing of coating is abundant.
Embodiment 2
One, the preparation of acrylic resin
The dilauroyl peroxide that accounts for monomer mass 3.5% is dissolved in the monomer, wherein methyl methacrylate, vinyl acetate, butyl methacrylate and 2-hydroxyethyl methacrylate consumption are respectively 82,18,20 and 42.8g, and the consumption of dimethylaminoethyl methacrylate is 15.7g.Slowly splash in the four-hole boiling flask that agitator, reflux condensing tube, thermometer are housed at 80 ℃ of following monomers, reaction medium is a toluene, and its consumption is 1.5 times of monomer mass, reacts 8 hours, and monomer conversion is reached more than 98%.
Two, acrylic resin modified preparation
The molecule mol ratio be 1: 1 isophorone diisocyanate and 2-hydroxyethyl methacrylate under the katalysis of 0.5wt% dibutyl tin laurate, 30 ℃ of reactions 6 hours down generate the isocyanic ester of band vinyl.The isocyanic ester of 42.4g synthetic band vinyl is added drop-wise in the synthetic acrylic resin, and under the effect of 0.6wt% octoate catalyst zinc, 60 ℃ were reacted 4 hours, added an amount of dehydrated alcohol, removed unreacted isocyanic ester, and vacuum extracts solvent.
Three, the preparation of ultraviolet light polymerization cathode electrophoresis dope
The adding mass ratio is 1: 1.5 2-methyl isophthalic acid-[4-methylthio phenyl]-2-morpholino acetone-1 and a 1-methylcyclohexane benzophenone photoinitiator in acrylic resin modified, its consumption is the 1.0wt% of resin, through the propionic acid pH value that neutralizes is 6.0, and to be diluted to solid content with deionized water be 15%, is mixed with the ultraviolet light polymerization cathode electrophoresis dope through high speed dispersion.
Four, ultraviolet light polymerization cathode electrophoresis dope Performance Detection
With the preparation the ultraviolet light polymerization cathode electrophoresis dope as electrophoresis groove liquid, under 25 ℃ of temperature, voltage 30V, the ABS plate that surperficial conductive processing is crossed carries out electrophoretic painting.60 ℃ of flash distillation 10min of model after the application, curing cross-linked is 60 seconds under room temperature, 1kW high pressure Hg lamp irradiation.Recording coat-thickness is 25 μ m, paint film appearance light, fine and smooth smooth, and pencil hardness 6H, the two-way wiping examination of acetone coating is not seen the loss of gloss phenomenon 150 times, shows that film curing is abundant.
The foregoing description is used for the present invention that explains, rather than limits the invention, and in the protection domain of spirit of the present invention and claim, any modification and change to the present invention makes all fall into protection scope of the present invention.
Claims (10)
1, a kind of ultraviolet light polymerization cathode electrophoresis dope, it is characterized in that it mainly is made up of 100 parts of vinyl that have a uV curable and acrylic resin modified, 0.1~10 part of photoinitiator and 200~2000 parts of deionized waters with amido of galvanic deposit.
2. ultraviolet light polymerization cathode electrophoresis dope according to claim 1, it is characterized in that, described acrylic resin modified acrylic resin by hydroxy functional groups reacts under catalyst action with the isocyanic ester that contains vinyl and forms, and the mol ratio of isocyanato is 1: 0.3~1.0 in described acrylic resin modified middle hydroxyl and the isocyanic ester.
3. according to claim 1 and 2 described ultraviolet light polymerization cathode electrophoresis dopes, it is characterized in that described photoinitiator is made up of one or more of benzophenone and derivative, methyl phenyl ketone and derivative thereof and st-yrax ethers and derivative thereof.
4. ultraviolet light polymerization cathode electrophoresis dope according to claim 2, it is characterized in that, described acrylic resin by 5~26wt% contain the acrylic ester monomer of tertiary amine groups, acrylic ester monomer, other acrylic ester monomer of 45~70wt% and the copolymerization under the initiator effect of 0~30wt% vinyl monomer of 15~30wt% hydroxyl forms.
5. ultraviolet light polymerization cathode electrophoresis dope according to claim 2 is characterized in that, described catalyzer is zinc octoate, ferric acetyl acetonade, dibutyl tin laurate or organic bismuth catalyst.
6, ultraviolet light polymerization cathode electrophoresis dope according to claim 2 is characterized in that, the product of the acrylate monomer reaction that the described isocyanic ester that contains vinyl is monoisocyanates or polyisocyanates and hydroxyl.
7. ultraviolet light polymerization cathode electrophoresis dope according to claim 4 is characterized in that, described initiator is azo-initiator or peroxide initiator.
8. the preparation method of the described ultraviolet light polymerization cathode electrophoresis dope of claim 1 is characterized in that, may further comprise the steps:
(1) preparation acrylic resin: 5~26wt% contains the acrylic ester monomer of tertiary amine groups, acrylic ester monomer, other acrylic ester monomer of 45~70wt% and the copolyreaction under the initiator effect of 0~30wt% vinyl monomer of 15~30wt% hydroxyl made.
(2) preparation is acrylic resin modified: acrylic resin and contain the isocyanic ester of vinyl or product prepared in reaction under catalyst action that the acrylate monomer of polyisocyanates and hydroxyl reacts, in the acrylic resin in hydroxyl and the isocyanic ester mol ratio of isocyanato be 1: 0.3~1.0.
(3) preparation ultraviolet light polymerization cathode electrophoresis dope: in acrylic resin modified, add photosensitizers,, and, be mixed with electrophoretic paint through high-speed stirring with the deionized water dilution with the acid neutralization.
9. preparation method according to claim 8 is characterized in that, described initiator is azo class or peroxide initiator; Described catalyzer is zinc octoate, ferric acetyl acetonade, dibutyl tin laurate or organic bismuth catalyst.
10. preparation method according to claim 8 is characterized in that, described acid is organic acid or mineral acid.
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CN104151890A (en) * | 2014-07-30 | 2014-11-19 | 中国海洋石油总公司 | Ultraviolet-curable cathode electrophoresis coating composition |
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